10 events found.
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2025 Downeast Challenge
The Marblehead Yacht Club invites sailors to participate in the Downeast Challenge, a long-distance overnight sailboat race of 80 nautical miles from Marblehead, Mass to Portland, Maine starting on Friday, July 25. This is a great way to get to Maine for summer cruising or challenge yourself with long distance overnight sailing; sailors can also …
2025 Courageous Sailing Annual Flip Flop Regatta
The Flip Flop Regatta is a fun and competitive race for all - one of the largest New England regattas of the season - a pursuit style race starting in Broad Sound, looping around the outer harbor islands, and finishing in inner Boston Harbor! The Flip Flop draws a 50+ boat fleet, all racing in support …